Studies will be continued toward basic methodology involving the cyclopropyl iminium ion rearrangement and variants thereof and coupling this process to sigmatropic rearrangements and other processes to rapidly assemble complex ring systems found in the alkaloids possessing a wide variety of pharmacological activity - specific applications will be undertaken to minovincine and lycodoline. Studies will be continued in the area of vinyl ether carbanions. New focus on preparation and study of tetrahydrooxepins and applications to the macrolides and other naturally occurring oxepane ring systems. New areas of study include 1) the design, synthesis and testing of a chiral (non racemic) ligand (non transferrable) for application to asymmetric synthesis using organocuprates: 2) design, synthesis and testing of a chiral auxiliary which will permit effective construction of quartenary carbons using Diels-Alder and alkylation reactions with good ee and in high chemical yield; 3) design synthesis and testing of a chiral auxiliary for Claisen rearrangements. Applications are planned in each of the above areas pending the outcome of preliminary studies now underway such as 1) solution of the side chain chirality problem for ceroplastol I and 2) synthesis of key intermediates for saudin among other systems.